Process for the production of 3-aryl-uracils

ABSTRACT

Aryl- or heteroaryluracils of formula I                    
     wherein R 1  signifies methyl or ethyl; R 2  signifies —CF 3 , —CClF 2 , —CCl 2 F, or —C 2 F 5 ; and Q is an aryl or heteroaryl group; are produced whereby a compound of formula II 
     
       
         O═C═N—Q  (II)  
       
     
     is reacted at a temperature of −5° C. to +40° C. with an enamine of formula III                    
     wherein R 19  signifies C 1 -C 6 -alkyl, in the presence of a solvent and of 0.1 to 0.4 equivalents of a base with respect to the employed enamine of formula III. The compounds of formula I are useful as herbicides. An example of the compounds of formula I is 2-chloro-5-(3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1-(2H)pyrimidinyl)-benzoic acid 1-aalyloxycarbonyl-1-methyl-ethyl-ester.

This is a continuation-in-part application of U.S. patent applicationSer. No. 08/935,778 filed on Sep. 23,1997.

The present invention relates to a new process for the production of3-phenyl-uracils, by reacting phenylisocyanates with N-alkyl-enamines.

From WO 95/17931, it is known that compounds of formulae A and B

wherein Z₁ and Z₂ denote oxygen or sulphur, whereby at least one of thegroupings denotes sulphur; Ry denotes hydrogen or alkyl, alkenyl,alkinyl or alkylcarbonyl, Rs denotes hydrogen, halogen, cyano oroptionally substituted alkyl, Rt denotes hydrogen or halogen, Rv denoteshalogen, cyano, nitro, amino or an aminoalkylsulphonylalkyl group and Rzdenotes alkyl or halogen-alkyl, may be produced in a manner whereby anenamine of formula C

wherein Rx denotes alkyl, is reacted with a cyanoaryliso(thio)cyanate offormula D

optionally in the presence of a reaction excipient and optionally in thepresence of a diluent.

The reactions disclosed specifically in the preparation examples arecarried out in a solvent mixture of dimethylformamide/toluene attemperatures of −70° C. or −15° C., whereby 1 equivalent of sodiumhydride is respectively used as base. The yields of only 9 or 25% oftheory attained in these reactions are however completely unsatisfactoryespecially for large scale usage.

It has now surprisingly been found that the yields of such reactions maybe increased considerably if the reaction is carried out in a specialsolvent in the presence of a defined quantity of certain selected basesin a narrowly restricted temperature range especially adapted thereto.

In accordance with the invention, it is therefore proposed thatcompounds of formula I

wherein

R₁ signifies methyl or ethyl;

R₂ signifies —CF₃, —CClF₂, —CCl₂F or —C₂F₅;

Q is a group

X and Y, independently of one another, are oxygen or sulphur;

R₃ signifies hydrogen, fluorine or chlorine;

R₄signifies hydrogen, fluorine, chlorine, bromine, cyano, nitro, methylor difluoromethyl;

R₅ signifies hydrogen, halogen, cyano, nitro, hydroxy, C₁₋₆-alkoxy,C₁₋₆-alkylthio, C₂₋₆-alkenyloxy,

C₂₋₆-alkinyloxy, C₁₋₆-halogenalkoxy, C₂₋₆halogen-alkenyloxy,C₂-E₈-alkylcarbonyl-alkoxy, C₂₋₈-alkoxycarbonylalkoxy,C₁₋₃-alkyl-oxiranylmethoxy,

C₄₋₈-alkenyloxycarbonylalkoxy or C₄₋₈-alkinyloxycarbonylaikoxy;

R₂₀ is hydrogen or C₁₋₄-alkyl;

R₂₁ and R₂₂, independently of one another, signify C₁₋₄-alkyl; or R₂₁and R₂₂ together signify a

C₂₋₃-alkylene bridge;

R₂₃ signifies cyano or COR₆;

R₂₄ signifies hydrogen or halogen;

R₆ signifies OH, C₁₋₆-alkoxy, C₂₋₆-alkenyloxy, C₂₋₆-alkinyloxy,C₂₋₈-alkoxyalkoxy, C₃₋₆-cycloalkoxy, C₃₋₆-cycloalkenyloxy,C₃₋₆-cycloalkyl-C₁₋₆-alkoxy, C₁₋₆-halogen-alkoxy,C₂₋₆-halogen-alkenyloxy, C₁₋₆-hydroxycarbonylalkoxy,C₃₋₈-alkoxycarbonylalkoxy, C₃₋₈-alkenyloxycarbonylalkoxy,C₃₋₈-alkinyloxycarbonylalkoxy, N(C₁l₃-alkyl)₂or N(C₃₋₄-alkenyl)₂;

R₇ signifies C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkinyl, C₂₋₈-alkoxyalkyl,C₃₋₆-cycloalkyl, C₁₋₆-halogen-alkyl, C₂₋₆-halogen-alkenyl,C₂₋₆-alkylsulfonyloxyalkyl, C₁₋₁₀-phenylsulfonyloxyalkyl, N(C₁₋₅-alkyl)₂or diallylamino;

R₈ signifies hydrogen, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkinyl,C₂-C₁₀-alkoxyalkyl, C₃₋₆-cycloalkyl, C₃₋₆-cycloalkenyl,C₁₋₆-halogen-alkyl, C₃₋₆-halogen-alkenyl, C₂₋₆-hydroxycarbonylalkyl,C₃₋₈-alkoxycarbonylalkyl, C₃₋₈-alkenyloxycarbonylalkyl orC₃₋₈-alkinyloxycarbonylalkyl;

R₉ signifies hydrogen, OH, CH₂COOR₁₅, CH₂CON(C₁₋₄-alkyl)₂,CH₂CON(C₃₋₄-alkenyl)₂, COOR₁₆, CON(C₃₋₄-alkyl)₂, CON(C₃₋₄-alkenyl)₂,C₁₋₆-alkyl, hydroxy-C₁₋₆-alkyl, C₂₋₁₀-alkoxycarbonyl-alkoxy orC₂₋₈-alkoxyalkyl;

R₁₀ signifies hydrogen, Cyano, C₁₋₆-alkyl, C₂₋₆alkenyl, C₂₋₆-alkinyl,hydroxy-C₁₋₆-alkyl, C₂₋₈-alkoxyalkyl, C₃₋₆-cycloalkyl,C₁₋₆-halogen-alkyl, COOR₁₇, CON(C₁₋₄-alkyl)₂ or CON(C₃₋₄-alkenyl)₂;

R₁₁ signifies hydrogen, C₁₋₆-alkyl or C₁₋₆-halogen-alkyl;

R₁₂ signifies hydrogen, C₁₋₆-alkyl, C₁₋₆-halogen-alkyl, CH₂OH,C₂₋₆-alkoxyalkyl, C₂₋₆-halogenalkoxyalkyl, COOR,₈, CON(C₁₄-alkyl)₂ orCON(C₃₋₄-alkenyl)₂;

R₁₃ signifies hydrogen, C₃₋₁₆-trialkylsilyloxy, C₁₋₆-alkoxy, chlorine,C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkinyl, C₃₋₆-cycloalkyl,C₃₋₆-cycloalkenyl, C₁₋₆-halogen-alkyl, C₂₋₆-halogen-alkenyl orC₁₋₆-hydroxycarbonylalkyl;

R₁₄ signifies hydrogen, C₁₋₆-alkyl or C₁₋₆-halogenalkyl;

R₁₅ signifies hydrogen, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkinyl,C₂₋₈-alkoxyalkyl, C₃₋₆-cycloalkyl, C₃₋₈-cycloalkenyl,C₁₋₆-halogen-alkyl, C₂₋₆-halogen-alkenyl, C₂₋₆-hydroxycarbonylalkyl,C₃₋₈-alkoxycarbonylalkyl, C₃₋₈-alkenyloxycarbonylalkyl orC₃₋₈-alkinyloxycarbonylalkyl;

R₁₆ signifies hydrogen, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkinyl,C₂₋₈-alkoxyalkyl, C₃₋₆-cycloalkyl, C₃₋₆-cycloalkenyl,C₁₋₆-halogen-alkyl, C₂₋₆-halogen-alkenyl, C₂₋₆-hydroxycarbonylalkyl,C₃₋₈-alkoxycarbonylalkyl, C₃₋₈-alkenyloxycarbonylalkyl orC₃₋₈-alkinyloxycarbonylalkyl;

R₁₇ signifies hydrogen, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkinyl,C₂₋₈-alkoxyalkyl, C₃₋₆-cycloalkyl, C₃₋₆-cycloalkenyl,C₁₋₆-halogen-alkyl, C₂₋₆-halogen-alkenyl, C₂ r-hydroxycarbonylalkyl,C₂₋₈-alkoxycarbonylalkyl, C₃₋₈-alkenyloxycarbonylalkyl orC₃₋₈-alkinyloxycarbonylalkyl; and

R₁₈ signifies hydrogen, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkinyl,C₂₋₈-alkoxyalkyl, C₃₋₆-cycloalkyl, C₃₋₆-cycloalkenyl,C₁₋₆-halogen-alkyl, C₂₋₆-halogen-alkenyl, C₂₋₆-hydroxycarbonylalkyl,C₃₋₈-alkoxycarbonylalkyl, C₃₋₈-alkenyloxycarbonylalkyl orC₃₋₈-alkinyloxycarbonylalkyl, are produced in a manner whereby acompound of formula II

O═C═N—Q  (II)

wherein Q has the significance given under formula I, is reacted at atemperature of −5° C. to +50° C. with an enamine of formula III

wherein R₁ and R₂ have the significances given under formula I, and R₁₉signifies C₁-C₆-alkyl, in pure dimethylformamide, dimethyl sulphoxide,acetonitrile, propionitrile, ethyl acetate, tetra-hydrofuran, dioxane,N-methylpyrrolidone, methyl-tert.-butylether, dimethylacetamide ortoluene or mixtures thereof as solvents, in the presence of 0.1 to 0.4equivalents of a base selected from potassium tert.butylate, sodiumtert.butylate, sodium methylate, sodium ethylate, potassium methylate,potassium ethylate, sodium hydride, potassium hydride, sodium pentylate,potassium pentylate and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU),preferably potassium tert.butylate and potassium tert.pentylate withrespect to the employed enamine of formula III.

The alkyl groups present in the definitions of substituents may bestraight-chain or branched, and denote for example methyl, ethyl,propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl or decyl, as well asthe branched isomers thereof. Alkoxy, alkylthio, halogen-alkyl,alkylamino, alkenyl and alkinyl groups are derived from the said alkylgroups. The alkenyl and alkinyl groups may be unsaturated once or manytimes. For definitions such as C₃₋₈-alkinylcarbonylalkyl, the carbonylatom is not counted as a carbon atom.

Appropriate cycloalkyl substituents contain 3 to 6 carbon atoms and aree.g. cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Correspondingcycloalkenyl substituents may be unsaturated once or also many times, asfor example cyclopentadienyl or cyclohexadienyl.

Halogen normally signifies fluorine, chlorine, bromine or iodine. Thesame also applies to halogen in conjunction with other significances,e.g. halogen-alkyl.

The preferred base in the process according to the invention ispotassium tert.butylate. The base is preferably used in an amount of 0.1to 0.4, preferably 0.15 to 0.3, especially 0.2 or 0.3 equivalents inrelation to the employed enamine of formula III. Amounts of base of 0.25to 0.35 and 0.2 to 0.4 equivalents are also suitable.

A preferred temperature range is 10° C. to 50° C., especially preferred20° C. to 40° C. Further suitable temperature ranges are −5° C. to +40°C., especially 0° C. to +20° C., in particular 0° C. to +5° C.

Addition of the reagents may be effected in various ways. For example,the base may be presented in pure dimethylformamide, dimethylsulphoxide, acetonitrile, propionitrile, ethyl acetate, tetrahydrofuran,dioxane, N-methylpyrrolidone, methyl-tert.-butylether, dimethylacetamideor toluene or mixtures thereof, the compound of formula III added andsubsequently the compound of formula II introduced, or the compound offormula III and II may be presented as a mixture and subsequently thebase in pure dimethylformamide, dimethyl sulphoxide, acetonitrile,propionitrile, ethyl acetate, tetrahydrofuran, dioxane,N-methylpyrrolidone, methyl-tert.-butylether, dimethylacetamide ortoluene or mixtures thereof is added, or the base is presented in puredimethylformamide, dimethyl sulphoxide, acetonitrile, propionitrile,ethyl acetate, tetrahydrofuran, dioxane, N-methylpyrrolidone,methyl-tert.-butylether, dimethylacetamide or toluene or mixturesthereof and subsequently a mixture of compound of formula III and IIadded. In a preferred variant of the process according to the invention,the base is presented in pure dimethylformamide, dimethyl sulphoxide,acetonitrile, propionitrile, ethyl acetate, tetrahydrofuran, dioxane,N-methylpyrrolidone, methyl-tert.-butylether, dimethylacetamide ortoluene or mixtures thereof and then the compound of formula III isadded, and afterwards the compound of formula II.

In order to attain the desired high selectivity of the reaction, theenamine of formula III is advantageously used in excess, and preferably4 equivalents of enamine of formula III are brought to react with 1equivalent of the isocyanate of formula II.

In the process according to the invention, preferably those compounds offormula I are produced wherein R₁ signifies methyl or ethyl; R₂signifies —CF₃, —CClF₂, —CCl₂F or —C₂F₅; Q is a group

X and Y, independently of one another, are oxygen or sulphur;

R₃ signifies hydrogen, fluorine or chlorine;

R₄ signifies hydrogen, fluorine, chlorine, bromine, cyano, nitro, methylor difluoromethyl;

R₅ signifies hydrogen, halogen, cyano, nitro, hydroxy, C₁₋₆-alkoxy,C₂₋₆-alkenyloxy, C₂₋₆-alkinyloxy, C₁₋₆-halogen-alkoxy,C₂₋₆-halogen-alkenyloxy, C₃₋₈-alkoxycarbonylalkoxy or C₁₋₆-alkylthio;

R₆ signifies hydrogen, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkinyl,C₂₋₈-alkoxyalkyl, C₃₋₆-cycloalkyl, C₃₋₆-cycloalkenyl,C₁₋₆-halogen-alkyl, C₂₋₆-halogen-alkenyl, C₁₋₆-hydroxycarbonylalkyl,C₃₋₈-alkoxycarbonylalkyl, C₃₋₈-alkenyloxycarbonylalkyl,C₃₋₈-alkinylcarbonylalkyl, C₂₋₆-dialkylenamino orC₃₋₈-dialkylenaminooxyalkyl;

R₇ signifies C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkinyl, C₂₋₈-alkoxyalkyl,C₃₋₆-cycloalkyl, C₁₋₆-halogen-alkyl, C₁₋₆-halogen-alkenyl,C₂₋₆-alkylsulfonyloxyalkyl, C₁₋₁₀-phenylsulfonyloxyalkyl,C₂₋₁₀-dialkylamino or diallylamino;

R₈ signifies hydrogen, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkinyl,C₃₋₆-cycloalkyl, C₃₋₆-cycloalkenyl, C₁₋₆-halogen-alkyl,C₁₋₆-halogen-alkenyl, C₂₋₆-hydroxycarbonylalkyl,C₃₋₈-alkoxycarbonylalkyl, C₂₋₈-alkenyloxycarbonylalkyl orC₃₋₈-alkinylcarbonylalkyl;

R₉ signifies hydrogen, CH₂COOR₁₅, COOR₁₋₆, C₁₋₆-alkyl orC₂₋₈-alkoxyalkyl;

R₁₀ signifies hydrogen, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkinyl,C₂₋₈-alkoxyalkyl, C₃₋₆-cycloalkyl, C₁₋₆-halogen-alkyl or COOR₁₇;

R₁₁ signifies hydrogen, C₁₋₆-alkyl or C₁₋₆-halogen-alkyl;

R₁₂ signifies hydrogen, C₁₋₆-alkyl, C₁₋₆-halogen-alkyl, CH₂OH,C₂₋₆-alkoxyalkyl, C₂₋₆-halogen-alkoxyalkyl or COOR₁₈;

R₁₃ signifies hydrogen, hydroxy, C₃₋₁ ₆-trialkylsilyloxy, C₁₋₆-alkoxy,chlorine, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkinyl, C₃₋₆-cycloalkyl,C₃₋₆-cycloalkenyl, C₁₋₆-halogen-alkyl, C₂₋₆-halo-alkenyl orC₁₋₆-hydroxycarbonylalkyl;

R₁₄ signifies hydrogen, C₁₋₆-alkyl or C₁₋₆-halogen-alkyl;

R₁₅ signifies hydrogen, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkinyl,C₂₋₈-alkoxyalkyl, C₃₋₆-cycloalkyl, C₃₋₆-cycloalkenyl,C₁₋₆-halogen-alkyl, C₂₋₆-halogen-alkenyl, C₂₋₆-hydroxycarbonylalkyl,C₃₋₈-alkoxycarbonylalkyl, C₃₋₈-alkenyloxycarbonylalkyl,C₃₋₈-alkinylcarbonylalkyl, C₂₋₆-dialkylamino, C₂₋₈-dialkyleneamino orC₃₋₈-dialkyleneaminooxyalkyl;

R₁₆ signifies hydrogen, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkinyl,C₂₋₈-alkoxyalkyl, C₃₋₆-cycloalkyl, C₃₋₆-cycloalkenyl,C₁₋₆-halogen-alkyl, C₂₋₆-halogen-alkenyl, C₂₋₆-hydroxycarbonylalkyl,C₃₋₈-alkoxycarbonylalkyl, C₃₋₈-alkenyloxycarbonylalkyl,C₃₋₈-alkinylcarbonylalkyl, C₂₋₆-dialkylamino, C₂₋₈-dialkyleneamino orC₃₋₈-dialkyleneaminooxyalkyl;

R₁₇ signifies hydrogen, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkinyl,C₂₋₈-alkoxyalkyl, C₃₋₆-cycloalkyl, C₃₋₆-cycloalkenyl,C₁₋₆-halogen-alkyl, C₂₋₆-halogen-alkenyl, C₂₋₆-hydroxycarbonylalkyl,C₃₋₈-alkoxycarbonylalkyl, C₃₋₈-alkenyloxycarbonylalkyl,C₃₋₈-alkinylcarbonylalkyl, C₂₋₆-dialkylamino, C₂₋₈-dialkyleneamino orC₃₋₈-dialkyleneaminooxyalkyl; and

R₁₈ signifies hydrogen, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkinyl,C₂₋₈-alkoxyalkyl, C₃₋₆-cycloalkyl, C₃₋₆-cycloalkenyl,C₁₋₆-halogen-alkyl, C₂₋₆-halogen-alkenyl, C₂₋₆-hydroxycarbonylalkyl,C₃₋₈-alkoxycarbonylalkyl, C₃₋₈-alkenyloxycarbonylalkyl,C₃₋₈-alkinylcarbonylalkyl, C₂₋₆-dialkylamino, C₂₋₈-dialkyleneamino orC₃₋₈-dialkyleneaminooxyalkyl, and it is characterised in that a compoundof formula II

O═C═N—Q  (II),

wherein Q has the significance given under formula I, is reacted at atemperature of −5° C. to +40° C. with an enamine of formula III

wherein R₁ and R₂ have the significance given under formula I, and R₁₉signifies C₁-C₆-alkyl, in pure dimethylformamide or dimethyl sulphoxideas the solvent and in the presence of 0.2 to 0.4 equivalents of a baseselected from potassium tert.butylate, sodium methylate and sodiumhydride.

In the process according to the invention, advantageously thosecompounds of formula I are produced wherein Q is Q₁, Q₂, Q₃ or Q₄. Theprocess according to the inventon is especially suitable for theproduction of the following compounds:

3-(2,5-difluoro-phenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione,

3-(2,4-difluoro-phenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione,

3-(4-chloro-2-fluoro-phenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione,

3-(5-bromo-4-chloro-2-fluoro-phenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione,

3-(4-chloro-2-fluoro-5-nitro-phenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione,

3-(4-chloro-5-cyano-2-fluoro-phenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione,

3-(5-methallyloxy-4-chloro-2-fluoro-phenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione,

3-[4-chloro-2-fluoro-5-(2-methyl-oxiranylmethoxy)-phenyl]-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione,

2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-benzoicacid isopropyl ester,

2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-benzoicacid isopropyl ester,

2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-benzoicacid 1-cyclopropyl-ethyl ester,

2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-benzoicacid 1-methoxycarbonyl-ethyl ester,

2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-benzoicacid 2-ethoxycarbonyl-1-methyl-ethyl ester,

2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-benzoicacid 1-carboxy-1-methyl-ethyl ester,

2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-benzoicacid 1-methyl-1-(1-methyl-allyloxycarbonyl)-ethyl ester,

2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-benzoicacid 1-methoxycarbonyl-1-methyl-ethyl ester,

N-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-phenyl]-N-methyl-methanesulfonamide,

N-allyl-N-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-phenyl]-methanesulfonamide,

Ethanesulfonic acid[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-phenyl]-ethyl-amide,

C-chloro-N-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-phenyl]-N-prop-2-ynyl-methanesulfonamide,

3-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-phenyl]-acrylicacid isopropyl ester,

3-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-phenyl]-acrylicacid ethyl ester,

3-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-phenyl]-acrylicacid allyl ester and

2-chloro-5-(3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1-(2H)pyrimidinyl)-benzoicacid 1-allyloxycarbonyl-1-methyl-ethylester.

Compounds of formula I are known from the following publications:

U.S. Pat. No. 5,183,492, EP-A-0 255 047, EP-A-0 195 346, WO 88/10254,EP-A-0 563 384, U.S. Pat. No. 5,523,278, WO 93/06090, EP-A-0 561 319,U.S. Pat. No. 5,169,431, EP-A-0 617 033, WO 95/33746, U.S. Pat. No.5,441,925, EP-A-0 705 829 and WO 95/17391.

Compounds of formula 11 are known for example from U.S. Pat. No.5,183,492 and EP-A-0 195 346.

The enamines of formula III may be produced for example whereby acompound of formula IV

is reacted with a compound of formula V

H—N—R₁  (V)

Reactions of this type are described for example in JP 05140060-A.

PREPARATION EXAMPLES Example H1

Preparation of2-chloro-5-(3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1-(2H)Pyrimidinyl)-benzoicacid 1-allyloxycarbonyl-1-methyl-ethyl-ester

0.347 g of potassium tert.butylate (content: 97%, 0.003 mols) aresuspended in 30 g of anhydrous dimethylformamide (water content <0.01%),and heated to a temperature of 40° C. Subsequently, 1.97 g of3-methylamino-4,4,4-trifluorobut-2-enoic acid ethyl ester (content:99.5%, 0.01 mols) are added at a temperature of 40 to 45° C., and thistemperature is maintained for a further 30 minutes, whereby a red-brownsolution is produced. After cooling the reaction mixture to atemperature of 0° C., 3.51 g of 5-isocyanato-2-chloro-benzoic acid1-allyloxycarbonyl-1-methyl-ethyl-ester (content: 97%, 0.0105 mols) aredispensed in over the course of 30 minutes, whereby the temperature ismaintained at between 0 and 5° C. After removing the cooling bath, theresultant dark brown solution is stirred for a further 30 minutes, andthe pH value of the now dark red solution is adjusted to pH 7 with 2.7 gof 1 M HCl [the content of2-chloro-5-(3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1-(2H)pyrimidinyl)-benzoicacid 1-allyloxyoarbonyl-1-methyl-ethyl-ester in this solution is 11%,which corresponds to a yield of 89%]. The solvent is subsequentlydistilled off in a rotary evaporator, and the residue (5.6 g) isrecrystallised in 12 g of isopropyl alcohol [the inorganic salts areremoved by hot filtration]. After drying in a vacuum drying chamber (60°C. for 12 hours), 4.10 g (86.3% of theory) of2-ohloro-5-(3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1-(2H)pyrimidinyl)-benzoicacid 1-allyloxycarbonyl-1-methyl-ethyl-ester are obtained in a contentof 99%.

Example H2

Preparation of2-chloro-5-(3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1-(2H)Pyrimidinyl)-benzoicacid 1-allyoxycarbonyl-1-methyl-ethyl-ester

0.347 g of potassium tert.butylate (content: 97%, 0.003 mols) aresuspended in 20 g of anhydrous dimethylformamide (water content <0.01%),and heated to a temperature of 40° C. Subsequently, 1.97 g of3-methylamino-4,4,4-trifluorobut-2-enoic acid ethyl ester (content:99.5%, 0.01 mols) are added at a temperature of 40 to 45° C., and thistemperature is maintained for a further 30 minutes, whereby a red-brownsolution is produced. After cooling the reaction mixture to atemperature of 0° C., 3.51 g of 5-isocyanato-2-chloro-benzoic acid1-allyloxycarbonyl-1-methyl-ethyl-ester (content: 97%, 0.0105 mols) aredispensed in over the course of 30 minutes, whereby the temperature ismaintained at between 0 and 50° C. After removing the cooling bath, theresultant dark brown solution is stirred for a further 30 minutes, andthe pH value of the now dark red solution is adjusted to pH 7 with 2.7 gof 1 M HCl [the content of2-chloro-5-(3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1-(2H)pyrimidinyl)-benzoicacid 1-allyloxycarbonyl-1-methyl-ethyl-ester in this solution is 13.1%,which corresponds to a yield of 79%]. The solvent is subsequentlydistilled off in a rotary evaporator, and the residue (5.4 g) isrecrystallised in 12 g of isopropyl alcohol [the inorganic salts areremoved by hot filtration]. After drying in a vacuum drying chamber (60°C. for 12 hours), 3.68 g (77.5% of theory) of2-chloro-5-(3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1-(2H)pyrimidinyl)-benzoicacid 1-allyloxycarbonyl-1-methyl-ethyl-ester are obtained in a contentof 98.6%.

Example H3

Preparation of2-chloro-5-(3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethvtl-1-(2H)Pvrimidinyl)-benzoicacid 1-allyloxycarbonyl-1-methyl-ethyl-ester

A suspension of 20 g of dry dimethylformamide (water content <0.01%) and0.347 g of potassium tert.butylate (content: 97%, 0.003 mols) is addedat a temperature of 0 to 5° C. to a mixture of 1.97 g of3-methylamino-4,4,4-trifluorobut-2-enoic acid ethyl-ester (content:99.5%, 0.01 mols) and 3.51 g of 5-isocyanato-2-chloro-benzoic acid1-allyloxycarbonyl-1-methyl-ethyl-ester (content: 97%, 0.0105 mols) insuch a manner that the temperature of the reaction mixture does notexceed 5° C. The pH value of the resultant dark red solution is adjustedto pH 7 with 2.6 g of 1 M HCl [the content of2-chloro-5-(3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1-(2H)pyrimidinyl)-benzoicacid 1-allyloxycarbonyl-1-methyl-ethyl-ester in this solution is 11.2%,which corresponds to a yield of 61.4%]. The solvent is subsequentlydistilled off in a rotary evaporator, and the residue (5.5 g) isrecrystallised in 10 g of isopropyl alcohol [the inorganic salts areremoved by hot filtration]. After drying in a vacuum drying chamber (60°C. for 12 hours), 2.75 g (58.1% of theory) of2-chloro-5-(3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1-(2H)pyrimidinyl)-benzoicacid 1-allyloxycarbonyl-1-methyl-ethyl-ester are obtained in a contentof 98.2%.

Example H4

Preparation of2-chloro-5-(3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1-(2H)Dvrimidinyl)-benzoicacid 1-allyloxycarbonyl-1-methyl-ethyl-ester

A mixture of 1.97 g of 3-methylamino-4,4,4-trifluorobut-2-enoic acidethyl-ester (content: 99.5%, 0.01 mols) and 3.51 g of5-isocyanato-2-chloro-benzoic acid1-allyloxycarbonyl-1-methyl-ethyl-ester (content: 97%, 0.0105 mols) isadded to a suspension of 20 g of dry dimethylformamide (water content<0.01%) and 0.347 g of potassium tert.butylate (content: 97%, 0.003mols) in such a manner that the temperature does not exceed 30° C. ThepH value of the resultant dark red solution is adjusted to pH 7 with 2.8g of 1 M HCl [the content of2-chloro-5-(3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1-(2H)pyrimidinyl)-benzoicacid 1-allyloxycarbonyl-1-methyl-ethyl-ester in this solution is 10.8%,which corresponds to a yield of 59.2%]. The solvent is subsequentlydistilled off in a rotary evaporator, and the residue (5.5 g) isrecrystallised in 10 g of isopropyl alcohol [the inorganic salts areremoved by hot filtration]. After drying in a vacuum drying chamber (60°C. for 12 hours), 2.75 g (58.1% of theory) of2-chloro-5-(3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1-(2H)pyrimidinyl)-benzoicacid 1-allyloxycarbonyl-1-methyl-ethyl-ester are obtained in a contentof 98.6%.

Example H5

Preparation of2-chloro-5-(3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1-(2H)pyrimidinyl)-benzoicacid 1-allyloxycarbonyl-1-methyl-ethyl-ester

1 g (0.0086 mols) of potassium tert.butylate is added whilst stirring,at room temperature, to a solution of 90 g of acetonitrile (watercontent <0.02%) and 17.7 g (0.088 mols) of3-methylamino-4,4,4-trifluorobut-2-enoic acid ethyl-ester. A clear,orange-red solution is produced, which is heated to 30° C. 14.3 g (0.044mols) of 5-isocyanato-2-chloro-benzoic acid1-allyloxycarbonyl-1-methyl-ethyl-ester in 28 g of acetonitrile aredispensed into this solution over 15 minutes, whereby the colour changesto dark green and afterwards to red. After this dispensing has takenplace, the reaction mixture is neutralised by adding 0.6 g (0.0091 mols)of acetic acid [the content of2-chloro-5-(3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1-(2H)pyrimidinyl)-benzoicacid 1-allyloxycarbonyl-1-methyl-ethyl-ester in this solution is 11.1%,which corresponds to a yield of 89%). Subsequently, the solvent isdistilled off at 50-55° C. and at 200-250 mbar pressure. Excess3-methylamino-4,4,4-trifluorobut-2-enoic acid ethyl-ester is separatedat 100-130° C. and at 5-10 mbar pressure, and the resulting oily residue(22.2 g) is taken up in 35 g of isopropanol. At 40° C., the salts aredissolved by adding 10 g of water, and the lower aqueous phase (10.5 g)is separated. The product is crystallised after adding a further 10 g ofwater at 30° C., and afterwards cooled to 5° C. After filtration anddrying the filter cake in a vacuum drying chamber (60° C. for 12 hours),18 g (85% of theory) of2-chloro-5-(3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1-(2H)pyrimidinyl)-benzoicacid 1-allyloxycarbonyl-1-methyl-ethyl-ester are obtained in a contentof 98.5%.

Example H6

Preparation of2-chloro-5-(3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1-(2H)Pyrimidinyl)-benzoicacid 1-allyloxycarbonyl-1-methyl-ethyl-ester

2.9 g of potassium tert.butylate (content 97%, 0.025 mols) are suspendedin 169 g of dry acetonitrile (water content <0.01%) and cooled to 0-5°C. Subsequently, at 0-5° C., 36.2 g of3-methylamino-4,4,4-trifluorobut-2-enoic acid isopropylester (content98.3%, 0.17 mols) are added and maintained at this temperature for 30minutes, whereby a red-brown solution is produced. Then, over the courseof 15 minutes, at 0-5° C., 27.3 g of 5-isocyanato-2-chloro-benzoic acid1-allyloxycarbonyl-1-methyl-ethyl-ester (content 99%, 0.084 mols) aredispensed in, whereby a dark brown solution is obtained. The latter isadjusted to pH 7 with 3.0 g of 1 N hydrochloric acid [content of desiredproduct in the solution is 15.5%, which corresponds to a yield of91.2%]. The solvent is subsequently distilled off in a vacuum, and theresidue (68 g) is recrystallised in 200 g of isopropyl alcohol, wherebythe inorganic salts are removed by hot filtration. After drying in avacuum drying chamber at 60° C. for 12 hours, 32.8 g (82% of theory) ofthe desired product are isolated in a content of 98.7%.

The compounds of formula I listed in the following tables may beproduced in analogous manner:

TABLE 1 Compounds of formula Ia (Ia)

physical Comp. No. R₁ R₂ R₃ R₄ R₅ data 1.01 CH₃ CF₃ —F —H —F 1.02 CH₃CF₃ —F —F —H 1.03 CH₃ CF₃ —F —Cl —H 1.04 CH₃ CF₃ —F —Cl —Br 1.05 CH₃ CF₃—F —Cl —I 1.06 CH₃ CF₃ —F —Cl —NO₂ 1.07 CH₃ CF₃ —Cl —Cl —H 1.08 CH₃ CF₃—F —CN —H 1.09 CH₃ CF₃ —F —Cl —CN 1.10 CH₃ CF₃ —F —Cl OCH₃ 1.11 CH₃ CF₃—F —Cl O-Allyl 1.12 CH₃ CF₃ —F —Cl O-Methallyl 1.13 CH₃ CF₃ —F —Cl

1.14 CH₃ CF₃ —F —Cl

1.15 CH₃ CF₃ —F —Cl —SCH₃ 1.16 CH₃ CF₃ —F —Cl

1.17 C₂H₅ CF₃ —H —CHF₂ —H 1.18 CH₃  C₂F₅ —H —CH₃ —H 1.19 CH₃ CF₃ —H —Cl

TABLE 2 Compounds of formula Ib (Ib)

Comp. No. R₁ R₂ R₃ R₄ R₆ physical data 2.01 CH₃ CF₃ —H —Cl

2.02 CH₃ CF₃ —F —Cl

2.03 CH₃ CF₃ —H —Cl

2.04 CH₃ CF₃ —H —Cl

2.05 CH₃ CF₃ —H —Cl

2.06 CH₃ CF₃ —H —Cl

2.07 CH₃ CF₃ —F —Cl

2.08 CH₃ CF₃ —H —Cl

2.09 CH₃ CF₃ —H —Cl

2.10 CH₃ CF₃ —H —Br

TABLE 3 Compounds of formula Ic (Ic)

Comp. No. R₁ R₂ R₃ R₄ R₇ R₈ physical data 3.01 CH₃ CF₃ —F —Cl —CH₃ —CH₃3.02 CH₃ CF₃ —F —Cl —CH₃ —Allyl 3.03 CH₃ CF₃ —F —Cl —C₂H₅ —C₂H₅ 3.04 CH₃CF₃ —F —Cl —CH₂Cl

3.05 CH₃ CF₃ —F —Cl

3.06 CH₃ CF₃ —F —Cl

3.07 CH₃ CF₃ —F —Cl —CF₃ —C₂H₅ 3.08 CH₃ CF₃ —H —Cl —C₂H₅ —H 3.09 CH₃ CF₃—F —Cl —C₂H₅ —H

TABLE 4 Compounds of formula Id (Id)

Comp. No. R₁ R₂ R₃ R₄ R₆ R₂₄ physical data 4.01 CH₃ CF₃ —F —Cl

—H 4.02 CH₃ CF₃ —F —Cl

—Cl 4.03 CH₃ CF₃ —F —Cl

—H 4.04 CH₃ CF₃ —F —Cl

—H 4.05 CH₃ CF₃ —F —Cl

—Br 4.06 CH₃ CF₃ —F —Cl

—H 4.07 CH₃ CF₃ —F —Cl

—H 4.08 CH₃ CF₃ —F —Cl

—Cl 4.09 CH₃ CF₃ —F —Cl

—H 4.10 CH₃ CF₃ —F —Cl

—Cl 4.11 CH₃ CF₃ —H —Cl —OCH₃ —H 4.12 CH₃ CF₃ —H —Cl —OCH₃ —Cl 4.13 CH₃CF₃ —H —H —OC₂H₅ —H 4.14 CH₃ CF₃ —H —H —OC₂H₃ —Cl

TABLE 5 Compounds of formula Ie (Ie)

Comp. No. R₁ R₂ R₃ R₉ X physical data 5.01 CH₃ CF₃ —F —COOCH₃ —O— 5.02CH₃ CF₃ —F —COOC₂H₅ —S— 5.03 CH₃ CF₃ —F —CH₂OH —O— 5.04 CH₃ CF₃ —F—CH₂OCH₃ —O— 5.05 CH₃ CF₃ —F —CH₂COOCH₃ —O— 5.06 CH₃ CF₃ —H—OCH(CH₃)COOCH₃ —O— 5.07 CH₃ CF₃ —F —OCH(CH₃)COOC₂H₅ —O— 5.08 CH₃ CF₃ —F—OH —O—

TABLE 6 Compounds of formula If (If)

Comp. physical No. R₁ R₂ R₃ R₄ R₁₀ Y data 6.01 CH₃ CF₃ —F —Cl —H —O—6.02 CH₃ CF₃ —F —Cl —CH₃ —O— 6.03 CH₃ CF₃ —F —Cl —C₂H₅ —O— 6.04 CH₃ CF₃—F —Cl —CH₃ —S— 6.05 CH₃ CF₃ —F —Cl —CH₃ —O— 6.06 CH₃ CF₃ —F —Cl —COOCH₃—O— 6.07 CH₃ CF₃ —F —Cl —CH₂OH —O— 6.08 CH₃ CF₃ —H —Cl —COOCH₃ —O— 6.09CH₃ CF₃ —H —Cl —CN —O—

TABLE 7 Compounds of formula Ig (Ig)

Comp. physical No. R₁ R₂ R₃ R₄ R₁₁ R₁₂ data 7.01 CH₃ CF₃ —F —Cl —H —CH₃7.02 CH₃ CF₃ —F —Cl —CH₃ —CH₃ 7.03 CH₃ CF₃ —F —Cl —CH₃ —CH₂OH 7.04 CH₃CF₃ —F —Cl —CH₃ —COOCH₃ 7.05 CH₃ CF₃ —F —Cl —H —COOCH₃ 7.06 CH₃ CF₃ —F—Cl —CH₃ —CH₂OCH₃ 7.07 CH₃ CF₃ —F —Cl —CH₃ —COOAllyl 7.08 CH₃ CF₃ —H —Cl—H —COOCH₃

TABLE 8 Compounds of formula Ih (Ih)

Comp. physical No. R₁ R₂ R₃ R₄ R₈ data 8.01 CH₃ CF₃ —F —Cl —CH₃ 8.02 CH₃CF₃ —F —Cl —C₂H₅ 8.03 CH₃ CF₃ —H —Cl —C₂H₅ 8.04 CH₃ CF₃ —F —Cl —Allyl8.05 CH₃ CF₃ —F —Cl

8.06 CH₃ CF₃ —F —Cl

8.07 CH₃ CF₃ —F —Cl

TABLE 9 Compounds of formula Ii (Ii)

Comp. physical No. R₁ R₂ R₃ R₄ R₁₁ R₁₄ data 9.01 CH₃ CF₃ —F —Cl —H —C₂H₅9.02 CH₃ CF₃ —F —Cl —CH₃ —CH₃  9.03 CH₃ CF₃ —F —Cl —CH₃ —C₂H₅ 9.04 CH₃CF₃ —H —Cl —CH₃ —CH₃ 

TABLE 10 Verbindungen der Formel Ik (Ik)

Comp. physical No. R₁ R₂ R₃ R₄ R₁₃ data 10.01 CH₃ CF₃ —F —Cl —CH₃ 10.02CH₃ CF₃ —F —Cl —OCH₃ 10.03 CH₃ CF₃ —F —Cl —OSi(CH₃)₃ 10.04 CH₃ CF₃ —F—Cl —Cl 10.05 CH₃ CF₃ —F —Cl —H 10.06 CH₃ CF₃ —H —Cl —H

TABLE 11 Compounds of formula Im (Im)

Comp. physical No. R₁ R₂ R₃ R₄ R₁₃ data 11.01 CH₃ CF₃ —F —Cl —CH₃ 11.02CH₃ CF₃ —F —Cl —OCH₃ 11.03 CH₃ CF₃ —F —Cl —OSi(CH₃)₃ 11.04 CH₃ CF₃ —F—Cl —Cl 11.05 CH₃ CF₃ —F —Cl —H 11.06 CH₃ CF₃ —H —Cl —H

TABLE 12 Compounds of formula In (In)

Comp. No. R₁ R₂ R₃ R₄ R₂₃ R₂₀ physical data 12.01 CH₃ CF₃ —F —Cl

—H 12.02 CH₃ CF₃ —F —Cl

—CH₃ 12.03 CH₃ CF₃ —F —Cl

—CH₃ 12.04 CH₃ CF₃ —F —Cl

—H 12.05 CH₃ CF₃ —F —Cl

—H 12.06 CH₃ CF₃ —F —Cl

—H 12.07 CH₃ CF₃ —F —Cl

—CH₃ 12.08 CH₃ CF₃ —H —Cl

—H 12.09 CH₃ CF₃ —H —H

—H

What is claimed is:
 1. In a process for the production of compounds ofthe formula I

wherein R₁ is methyl or ethyl; R₂ is —CF₃, —CClF₂, —CCl₂F or —C₂F₅; andQ is a group

X and Y, independently of one another, are oxygen or sulphur; R₃signifies hydrogen, fluorine or chlorine; R₄ signifies hydrogen,fluorine, chlorine, bromine, cyano, nitro, methyl or difluoromethyl; R₅signifies hydrogen, halogen, cyano, nitro, hydroxy, C₁₋₆-alkoxy,C₁₋₆-alkylthio, C₂₋₆-alkenyloxy, C₂₋₆-alkinyloxy, C₁₋₆-halogenalkoxy,C₂₋₆halogen-alkenyloxy, C₂₋₈-alkylcarbonyl-alkoxy,C₂₋₈-alkoxycarbonylalkoxy, C₁₋₃-alkyl-oxiranylmethoxy,

 C₄₋₈-alkenyloxycarbonylalkoxy or C₄₋₈-alkinyloxycarbonylalkoxy; R₂₀ ishydrogen or C₁₋₄-alkyl; R₂₁ and R₂₂, independently of one another,signify C₁₋₄-alkyl; or R₂₁ and R₂₂ together signify a C₂₃-alkylenebridge; R₂₃ signifies cyano or COR₆; R₂₄ signifies hydrogen or halogen;R₆ signifies OH, C₁₋₆-alkoxy, C₂₋₆-alkenyloxy, C₂₋₆-alkinyloxy,C₂₋₈-alkoxyalkoxy, C₃₋₆-cycloalkoxy, C₃₋₆-cycloalkenyloxy,C₃₋₆-cycloalkyl-C₁₋₆-alkoxy, C₁₋₆-halogen-alkoxy,C₂₋₆-halogen-alkenyloxy, C₁₋₆-hydroxycarbonylalkoxy,C₃₋₈-alkoxycarbonylalkoxy, C₃₋₈-alkenyloxycarbonylalkoxy,C₃₋₈-alkinyloxycarbonylalkoxy, N(C₁₋₃-alkyl)₂ or N(C₃₋₄-alkenyl)₂; R₇signifies C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkiny], C₂₋₈-alkoxyalkyl,C₃₋₆-cycloalkyl, C₁₋₆-halogenalkyl, C₂₋₆-halogen-alkenyl,C₂₋₆-alkylsulfonyloxyalkyl, C₁₋₁₀-phenylsulfonyloxyalkyl, N(C₁₋₅-alkyl)₂or diallylamino; R₈ signifies hydrogen, C₁₋₆-alkyl, C₂₋₆-alkenyl,C₂₋₆-alkinyl, C₂-C₁₀-alkoxyalkyl, C₃₋₆-cycloalkyl, C₃₋₆-cycloalkenyl,C₁₋₆-halogen-alkyl, C₃₋₆-halogen-alkenyl, C₂₋₆-hydroxycarbonylalkyl,C₃₋₈-alkoxycarbonylalkyl, C₃₋₈-alkenyloxycarbonytalkyl orC₃₋₈-alkinyloxycarbonylalkyl; R₉ signifies hydrogen, OH, CH₂COOR₁₅,CH₂CON(C₁₋₄-alkyl)₂, CH₂CON(C₃₋₄-alkenyl)₂, COOR₁₆, CON(C₁₋₄-alkyl)₂,CON(C₃₋₄-alkenyl)₂, C₁₋₆-alkyl, hydroxy-C₁₋₆-alkyl,C₂₋₁₀-alkoxycarbonyl-alkoxy or C₂,₈-alkoxyalkyl; R₁₀ signifies hydrogen,Cyano, C ₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkinyl, hydroxy-C₁₋₆-alkyl,C₂₋₈-alkoxyalkyl, C₃₋₆-cycloalkyl, C₁₋₆-halogen-alkyl, COOR₁₇,CON(C₁₋₄-alkyl)₂ or CON(C₃₋₄-alkenyl)₂; R₁₁ signifies hydrogen,C₁₋₆-alkyl or C₁₋₆-halogen-alkyl; R₁₂ signifies hydrogen, C₁₋₆-alkyl,C₁₋₆-halogen-alkyl, CH₂OH, C₂₋₆-alkoxyalkyl, C₂₋₆-halogenalkoxyalkyl,COOR₁₈, CON(C₁₋₄-alkyl)₂ or CON(C₃₋₄-alkenyl)₂; R₁₃ signifies hydrogen,C₃₋₁₆-trialkylsilyloxy, C₁₋₆-alkoxy, chlorine, C₁₋₆-alkyl, C₂₋₆-alkenyl,C₂₋₆-alkinyl, C₃₋₆-cycloalkyl, C₃₋₆-cycloalkenyl, C₁₋₆-halogen-alkyl,C₂₋₆-halogen-alkenyl or C₁₋₆-hydroxycarbonylalkyl; R₁₄ signifieshydrogen, C₁₋₆-alkyl or C₁₋₆-halogenalkyl; R₁₅ signifies hydrogen,C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkinyl, C₂₋₈-alkoxyalkyl,C₃₋₆-cycloalkyl, C₃₋₆-cycloalkenyl, C₁₋₆-halogen-alkyl,C₂₋₆-halogen-alkenyl, C₂₋₆-hydroxycarbonylalkyl,C₃₋₈-alkoxycarbonylalkyl, C₃₋₈-alkenyloxycarbonylalkyl orC₃₋₈-alkinyloxycarbonylalkyl; R₁₆ signifies hydrogen, C₁₋₆-alkyl,C₂₋₆-alkenyl, C₂₋₆-alkinyl, C₂₋₈-alkoxyalkyl, C₃₋₆-cycloalkyl,C₃₋₆-cycloalkenyl, C₁₋₆-halogen-alkyl, C₂₋₆-halogen-alkenyl,C₂₋₆-hydroxycarbonylalkyl, C₃₋₈-alkoxycarbonylalkyl,C₃₋₈-alkenyloxycarbonylalkyl or C₃₋₈-alkinyloxycarbonylalkyl; R₁₇signifies hydrogen, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkinyl,C₂₋₈-alkoxyalkyl, C₃₋₆-cycloalkyl, C₃₋₆-cycloalkenyl,C₁₋₆-halogen-alkyl, C₂₋₆-halogen-alkenyl, C₂₋₆-hydroxycarbonylalkyl,C₂₋₈-alkoxycarbonylalkyl, C₃₋₈-alkenyloxycarbonylalkyl orC₃₋₈-alkinyloxycarbonylalkyl; and R₁₈ signifies hydrogen, C₁₋₆-alkyl,C₂₋₆-alkenyl, C₂₋₆-alkinyl, C₂₋₈-alkoxyalkyl, C₃₋₆-cycloalkyl,C₃₋₆-cycloalkenyl, C₁₋₆-halogen-alkyl, C₂₋₆-halogen-alkenyl,C₂₋₆-hydroxycarbonylalkyl, C₃₋₈-alkoxycarbonylalkyl,C₃₋₈-alkenyloxycarbonylalkyl or C₃₋₈-alkinyloxycarbonylalkyl; byreacting an isocyanate of the formula II O═C═N—Q  (II) wherein Q has themeaning given under formula I, with an enamine of the formula III, at atemperature −5° C. to +50° C.

wherein R₁ and R₂ have the meanings given under formula I in thepresence of a base and in the presence of an inert solvent; theimprovement which comprises carrying out the reaction of the isocyanateof the formula II with the enamine of the formula III in the presence of0.1 to 0.3 equivalents of a base selected from potassium tert.butylate,sodium tert.butylate, sodium methylate, sodium ethylate, potassiummethylate, potassium ethylate, sodium hydride, potassium hydride, sodiumpentylate, potassium pentylate and 1,8-diazabicyclo[5.4.0]undec-7-ylene(DBU).
 2. Process according to claim 1, characterised in that the baseis used in a quantity of 0.2 to 0.3 equivalents and the compound offormula II is reacted at a temperature of −5° C. to +40° C. with anenamine of formula III.
 3. Process according to claim 1 for theproduction of compounds of formula I, wherein R₁ signifies methyl orethyl; R₂ signifies —CF₃, —CClF₂, —CCl₂F or —C₂F₅; Q is a group

X and Y, independently of one another, are oxygen or sulphur; R₃signifies hydrogen, fluorine or chlorine; R₄signifies hydrogen,fluorine, chlorine, bromine, cyano, nitro, methyl or difluoromethyl; R₅signifies hydrogen, halogen, cyano, nitro, hydroxy, C₁₋₆-alkoxy,C₂₋₆-alkenyloxy, C₂₋₆-alkinyloxy, C₁₋₆-halogenalkoxy,C₂₋₆halogen-alkenyloxy, C₃₋₈-alkoxycarbonyl-alkoxy or C₁₋₆-alkylthio; R₆signifies hydrogen, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkinyl,C₂₋₈-alkoxyalkyl, C₃₋₆-cycloalkyl, C₃₋₆-cycloalkenyl,C₁₋₆-halogen-alkyl, C₂₋₆-halogen-alkenyl, C₁₋₆-hydroxycarbonylalkyl,C₃₋₈-alkoxycarbonylalkyl, C₃₋₈-alkenyloxycarbonylalkyl,C₃₋₈-akinylcarbonylalkyl, C₂₋₆-dialkylenamino orC₃₋₈-dialkylenaminooxyalkyl; R₇ signifies C₁₋₆-alkyl, C₂₋₆-alkenyl,C₂₋₆-alkinyl, C₂₋₈-alkoxyalkyl, C₃₋₆-cycloalkyl, C₁₋₆-halogenalkyl,C₁₋₆-halogen-alkenyl, C₂₋₆-alkylsulfonyloxyalkyl,C-₁₋₁₀-phenylsulfonyloxyalkyl, C₂₋₁₀-dialkylamino or diallylamino; R₈signifies hydrogen, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkinyl,C₃₋₆-cycloalkyl, C₃₋₆-cycloalkenyl, C₁₋₆-halogen-alkyl,C₁₋₆-halogen-alkenyl, C₂₋₆-hydroxycarbonylalkyl,C₃₋₈-alkoxycarbonylalkyl, C₂₋₈-alkenyloxycarbonylalkyl orC₃₋₈-alkinylcarbonylalkyl; R₉ signifies hydrogen, CH₂COOR₁₅, COOR₁₆,C₁₋₆-alkyl or C₂₋₈-alkoxyalkyl; R₁₀ signifies hydrogen, C₁₋₆-alkyl,C₂₋₆-alkenyl, C₂₋₆-alkinyl, C₂₋₈-alkoxyalkyl, C₃₋₆-cycloalkyl,C₁₋₆-halogen-alkyl or COOR₁₇; R₁₁ signifies hydrogen, C₁₋₆-alkyl orC₁₋₆-halogen-alkyl; R₁₂ signifies hydrogen, C₁₋₆-alkyl,C₁₋₆-halogen-alkyl, CH₂OH, C₂₋₆-alkoxyalkyl, C₂₋₆-halogen-alkoxyalkyl orCOOR₁₈; R₁₃ signifies hydrogen, hydroxy, C₃₋₁₆-trialkylsilyloxy,C₁₋₆-alkoxy, chlorine, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkinyl,C₃₋₆-cycloalkyl, C₃₋₆-cycloalkenyl, C₁₋₆-halogen-alkyl,C₂₋₆-halo-alkenyl or C₁₋₆-hydroxycarbonylalkyl; R₁₄ signifies hydrogen,C₁₋₆-alkyl or C₁₋₆-halogen-alkyl; R₁₅ signifies hydrogen, C₁₋₆-alkyl,C₂₋₆-alkenyl, C₂₋₆-alkinyl, C₂₋₈-alkoxyalkyl, C₃₋₆-cycloalkyl,C₃₋₆-cycloalkenyl, C₁₋₆-halogen-alkyl, C₂₋₆-halogen-alkenyl,C₂₋₆-hydroxycarbonylalkyl, C₃₋₈-alkoxycarbonylalkyl,C₃₋₈-alkenyloxycarbonylalkyl, C₃₋₈-alkinylcarbonylalkyl,C₂₋₆-dialkylamino, C₂₋₈-dialkyleneamino or C₃₋₈-dialkyleneaminooxyalkyl;R₁₆ signifies hydrogen, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkinyl,C₂₋₈-alkoxyalkyl, C₃₋₆-cycloalkyl, C₃₋₆-cycloalkenyl,C₁₋₆-halogen-alkyl, C₂₋₆-halogen-alkenyl, C₂₋₆-hydroxycarbonylalkyl,C₃₋₈-alkoxycarbonylalkyl, C₃₋₈-alkenyloxycarbonylalkyl,C₃₋₈-alkinylcarbonylalkyl, C₂₋₆-dialkylamino, C₂₋₈-dialkyleneamino orC₃₋₈-dialkyleneaminooxyalkyl; R₁₇ signifies hydrogen, C₁₋₆-alkyl,C₂₋₆-alkenyl, C₂₋₆-alkinyl, C₂₋₈-alkoxyalkyl, C₃₋₆-cycloalkyl,C₃₋₆-cycloalkenyl, C₁₋₆-halogen-alkyl, C₂₋₆-halogen-alkenyl,C₂₋₆-hydroxycarbonylalkyl, C₃₋₈-alkoxycarbonylalkyl,C₃₋₈-alkenyloxycarbonylalkyl, C₃₋₈-alkinylcarbonylalkyl,C₂₋₆-dialkylamino, C₂₋₈-dialkyleneamino or C₃₋₈-dialkyleneaminooxyalkyland R₁₈ signifies hydrogen, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆-alkinyl,C₂₋₈-alkoxyalkyl, C₃₋₆-cycloalkyl, C₃₋₆-cycloalkenyl,C₁₋₆-halogen-alkyl, C₂₋₆-halogen-alkenyl, C₂₋₆-hydroxycarbonylalkyl,C₃₋₈-alkoxycarbonylalkyl, C₃₋₈-alkenyloxycarbonylalkyl,C₃₋₈-alkinylcarbonylalkyl, C₂₋₆-dialkylamino, C₂₋₈-dialkyleneamino orC₃₋₈-dialkyleneaminooxyalkyl, characterised in that a compound offormula II O═C═N—Q  (II) wherein Q has the significance given underformula I, is reacted at a temperature of −5° C. to +40° C. with anenamine of formula III

wherein R₁ and R₂ have the significances given under formula I, and R₁₉signifies C₁-C₆-alkyl, in pure dimethylformamide or dimethyl sulphoxideas the solvent, in the presence of 0.2 to 0.3 equivalents of a baseselected from potassium tert.butylate, sodium methylate and sodiumhydride.
 4. Process according to claim 1, characterised in thatpotassium tert.butylate is used.
 5. Process according to claim 1,characterised in that the base is used in a quantity of 0.15 to 0.3equivalents with respect to the employed enamine of formula III. 6.Process according to claim 5, characterised in that the base is employedin a quantity of 0.2 or 0.3 equivalents.
 7. Process according to claim1, characterised in that the reaction is carried out at a temperature of20° C. to +40° C.
 8. Process according to claim 1, characterised in thatthe reaction is carried out in a manner whereby the base is presented inpure dimethylformamide, dimethyl sulphoxide, acetonitrile,propionitrile, ethyl acetate, tetrahydrofuran, dioxane,N-methylpyrrolidone, methyl-tert.-butyl ether, dimethylacetamide ortoluene, or mixtures thereof, and then the compound of formula III isadded, and subsequently the compound of formula II is added.
 9. Processaccording to claim 1 for the production of compounds of formula I,wherein Q denotes Q₁, Q₂, Q₃ or Q₄.
 10. Process according to claim 1 forthe production of3-(2,5-difluoro-phenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione,3-(2,4-difluoro-phenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione,3-(4-chloro-2-fluoro-phenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione,3-(5-bromo-4-chloro-2-fluoro-phenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione,3-(4-chloro-2-fluoro-5-nitro-phenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione,3-(4-chloro-5-cyano-2-fluoro-phenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione,3-(5-methallyloxy-4-chloro-2-fluoro-phenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione,3-[4-chloro-2-fluoro-5-(2-methyl-oxiranylmethoxy)-phenyl]-1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione,2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-benzoicacid isopropyl ester,2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-benzoicacid isopropyl ester,2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-benzoicacid 1-cyclopropyl-ethyl ester,2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-benzoicacid 1-methoxycarbonyl-ethyl ester,2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-benzoicacid 2-ethoxycarbonyl-1-methyl-ethyl ester,2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-benzoicacid 1-carboxy-1-methyl-ethyl ester,2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-benzoicacid 1-methyl-1-(1-methyl-allyloxycarbonyl)-ethyl ester,2-chloro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-benzoicacid 1-methoxycarbonyl-1-methyl-ethyl ester,N-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-phenyl]-N-methyl-methanesulfonamide,N-allyl-N-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-phenyl]-methanesulfonamide,Ethanesulfonic acid[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-phenyl]-ethyl-amide,C-chloro-N-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-phenyl]-N-prop-2-ynyl-methanesulfonamide,3-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-phenyl]-acrylicacid isopropyl ester,3-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-phenyl]-acrylicacid ethyl ester,3-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidin-1-yl)-phenyl]-acrylicacid allyl ester and2-chloro-5-(3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1-(2H)pyrimidinyl)-benzoicacid 1-allyloxycarbonyl-1-methyl-ethylester.